4.9
(5549)
18,472
riders
02:48
54.4km
680m
Road cycling
Cycle the moderate 33.8-mile Middletown Valley loop, enjoying rolling hills, rural landscapes, and scenic creeks like Catoctin Creek.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
14.3 km
Highlight • River
Tip by
54.4 km
End point
Parking
Way Types & Surfaces
Way Types
30.5 km
23.8 km
< 100 m
Surfaces
32.2 km
22.1 km
< 100 m
< 100 m
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Elevation
Highest point (270 m)
Lowest point (110 m)
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Weather
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Today
Monday 8 June
27°C
17°C
0 %
Additional weather tips
Max wind speed: 19.0 km/h
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This route was planned by komoot.
This specific Middletown Valley loop is rated as moderate for road cycling. While the broader Middletown Valley is known for easier, shorter routes like the 'Middletown Lollipop', this 54.4 km (33.8 mi) route includes approximately 682 meters (2,237 feet) of elevation gain, making it a good challenge for cyclists with some experience.
The route primarily follows rural roads through the Middletown Valley. You can expect a landscape characterized by rolling hills, which contribute to the moderate elevation changes throughout the ride. The roads are generally well-suited for race bikes.
The Middletown Valley loop offers picturesque rural landscapes, including lush pastures, thriving dairy farms, and charming countryside. You'll also pass by scenic creeks, such as Catoctin Creek. The valley itself is renowned for its natural beauty, with views that have been historically praised.
Specific parking areas for this exact loop are not detailed in the tour data. However, as a popular cycling area, you can typically find parking in or around Middletown, Maryland, often near local parks or public spaces. It's advisable to check local regulations for parking availability before your visit.
Given its moderate difficulty, 54.4 km distance, and 682 meters of elevation gain, this specific loop might be challenging for absolute beginners. However, cyclists with some road cycling experience and a reasonable fitness level should find it enjoyable. For a more relaxed ride in the area, consider shorter, easier routes within the Middletown Valley.
The best times to cycle this route are typically spring and fall. During these seasons, the weather is generally mild, offering comfortable temperatures for cycling and beautiful scenery, whether it's spring blossoms or autumn foliage. Summer can also be pleasant, but be prepared for potentially warmer temperatures and higher humidity.
As this is a road cycling route primarily on public roads, dogs are generally permitted in public spaces along the route, provided they are on a leash and under control. However, it's not a traditional 'trail' where dogs might run freely. Always ensure your dog's safety and adhere to local leash laws and regulations.
No, you do not need any special permits or have to pay an entrance fee to cycle the Middletown Valley loop. It utilizes public roads and is freely accessible to cyclists.
While the route itself traverses rural areas, the town of Middletown, Maryland, which serves as a likely starting and ending point, offers various amenities. You can find cafes, pubs, and local accommodation options there to refuel or stay overnight. The broader Middletown Valley also features several wineries with scenic views.
For this moderate road cycling loop, it's recommended to bring plenty of water, snacks, a repair kit (spare tube, pump, tire levers), appropriate cycling attire, sun protection, and a helmet. A GPS device or a printed map of the route would also be beneficial, as cell service can be spotty in rural areas.
Yes, this route briefly intersects with or runs parallel to very small sections of other paths. Specifically, it touches parts of the Red Trail (1%), the Middletown Primary School / Cone Branch Trail (1%), and the Bear Spring Cabin Trail (1%). However, these are minor overlaps, and the primary experience is the dedicated Middletown Valley loop.
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